Cesium fluoride → HCID 11191016, compound

HRID 1513856Notes

Reaction equation

HRID 1513856 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2.[F:37][C:38]1[C:43]([F:44])=[CH:42][CH:41]=[CH:40][C:39]=1B(O)O.[F-].[Cs+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:37][C:38]1[C:43]([F:44])=[CH:42][CH:41]=[CH:40][C:39]=1[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 75806TricyclohexylphosphineHCID 2734333(2,3-Difluorophenyl)boronic acidHCID 116133766-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 11191016HCID 11191016, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Using the procedure demonstrated in Example 9, react trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (800 mg, 1.52 mmol), 2,3-difluorobenzene boronic acid (720 mg, 4.57 mmol), cesium fluoride (2.1 g, 13.7 mmol), palladium(II)acetate (34 mg, 0.15 mmol) and tricyclohexylphosphine (64 mg, 0.23 mmol) to obtain 622 mg (84%) of the title compound: mass spectrum (ion spray) 490.4 (M+H).

Sources & evidence

ORD record
ord-4ae50a7d1fc14ade85ece8b2035422e2
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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